Joining Dropbox

“You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something – your gut, destiny, life, karma, whatever. Because believing that the dots will connect down the road will give you the confidence to follow your heart even when it leads you off the well worn path; and that will make all the difference.”

Steve Jobs, Stanford University, June 2005

In 2012, I was seriously considering becoming a full time investor.

I’ve always loved startups and venture capital, and I had been fortunate enough after leaving LinkedIn to have a chance to work for Greylock Partners, one of the most successful firms in the industry.

In May of 2012, my daughter was born. While on parental leave, I remember receiving a note about a Greylock company that was looking to add to its executive team. I had visited that company just the month before, to help advise on strategies for organizing and executing on viral growth.

The role itself wasn’t the right fit, but for some reason that company stuck in my head. Did I really want to become a full time investor? Or did I want to go help build a company?

As it turns out, the company that I couldn’t get out of my head was Dropbox.

First moments after the birth of my daughter, May 2012.

Opportunity at Scale

Over my career, I’ve had the good fortune to work at three companies that grew to reach over 100 million users. After spending the past six years focused on building new companies, I’m excited about jumping back into the challenges of designing and shipping features for the more than 500 million people who use Dropbox to get things done.

With the proliferation of devices and ubiquitous connectivity of the modern workplace, I think there is a unique opportunity, right now, to help teams unleash their creative energy and find more enlightened ways of working together.

Drew has done a great job of sharing the high level vision for Dropbox, and I’m excited to dive into a space that has so much product potential.  The era of walled gardens is over, and there has been an explosion of new applications and content types in the past few years. The challenge is to design an open ecosystem that helps bring all of those capabilities together in a way that doesn’t sacrifice simplicity in design.

Connecting the Dots

For now, I just want to say thank you John Lilly for reconnecting me to the Dropbox team, and thank you to QuentinDrew, and the entire Dropbox team for this opportunity. It is truly amazing how life connects the dots.

2017: New Year, New Template, More Posts

2017 is finally here.

Over the past few years, there haven’t been many posts on my personal blog. Most of my writing time was dedicated to pieces for Wealthfront, although some of the drop off is likely do to the 140-character competition from Twitter.

Despite the drop off, I’ve been reviewing my blog posts from 2013 & 2014, and they seem to stand up quite well.

Starbucks even implemented almost all of the features I asked for in Dear Starbucks Mobile (2014)

So I’ve decided to dive back in. Topics will likely cover the same breadth of previous years: technology, strategy, finance, product, design & venture are all fair game.

I even updated the blog template to make sure my graphics are in line with the most recent version of Mac OS X.

New Year, New Template, More Posts.

The Executive in Residence (EIR) Series

It’s hard to believe, but it is now exactly six months since I left my role as an Executive in Residence at Greylock Partners, and joined Weathfront as COO.

Diving into a startup is all encompassing, but over the past few months quite a few people have asked me questions about the Executive in Residence (EIR) role.  Some of these people have had offers to become EIRs, others are curious about the role and whether they should pursue it as a career option.  For most, however, it’s just genuine curiosity  the EIR role is largely a low volume, undocumented role that is very unique to the private equity & venture capital ecosystems.

One of the guide posts for this blog has been a dedicated effort to take the questions that I receive regularly, and translate them into thoughtful and useful content to be broadly shared.  So before my experiences of 2012 fade into the shrouds of history, I’ve decided to write a quick series about my experience as an EIR, and the most common questions I’ve received.

The series will cover the following questions:

  1. What is an Executive in Residence (EIR)?
  2. Should I be an Executive in Residence (EIR)?
  3. How do you get an Executive in Residence (EIR) role?
  4. Challenges of being an Executive in Residence (EIR)
  5. Did you like being an Executive in Residence (EIR)?

As always, I’m hopeful that the information will be both interesting and even useful.

First Day at Wealthfront & Disclosures

Tomorrow is my first day at Wealthfront, and I couldn’t be more excited.

WF Logo New

As many long time readers know, personal finance has always been a passion of mine.  However, now that I’m moving from this being a personal passion to a professional role, there are some important disclosures that have to be made.

First, it needs to be stated that Psychohistory is my personal blog and is not written in my capacity as COO of Wealthfront Inc.  Nothing on this blog should be construed as, nor is it intended to be, personal investment advice.  The content of this blog represents my own views and/or opinions and does not represent the views and/or opinions of Wealthfront Inc.

Second, I’ve added a Disclosure tab to this blog, to ensure that at any time, any new visitor will have quick access to this information.

Third, none of the historical content of this blog is being modified from its original.  Those articles were written for purely personal reasons, and are appropriate for the time they were published.  That being said, going forward, I’m only going to publish content related to personal finance and investing through the official Wealthfront blog.  Wealthfront has published a fantastic series of articles on a wide range of topics, and I feel privileged to be added as one of the contributing authors there.

I will continue to blog here about personal topics of interest, including product management, design, software development, Silicon Valley, startups, tech tips, science, and of course coins.

Can’t wait to get started tomorrow.

Apple & Dow 15000: Update

In February 2012, I wrote a blog post that indicted the Dow Jones Industrial Average for including Cisco in 2009 instead of Apple.  At the time, Apple had just crossed $500 per share, and that simple decision had cost the US the psychology of an index hitting new highs.

I was driving home on Sunday, listening to the radio, and it occurred to me how different the financial news would be if Apple ($AAPL) was in the Dow Jones Industrial Average (^DJI).

Of course, being who I am, I went home and built a spreadsheet to recalculate what would have happened if Dow Jones had decided to add Apple to the index instead of Cisco back in 2009.  Imagine my surprise to see that the Dow be over 2000 points higher.

Update: AAPL at $700

With the launch of the iPhone 5, we find ourselves roughly 7 months later.  For fun, I re-ran the spreadsheet that calculated what the DJIA would be at if they had added AAPL to the index in 2009 instead of CSCO. (To date, I’ve never seen an explanation on why Cisco was selected to represent computer hardware instead of Apple.)

Result: Dow 16,600

As of September 17, 2012, AAPL closed at 699.781/share.  As it turns out, if Dow Jones had added Apple instead of Cisco in 2009, the index would now be at 16,617.82.  Hard to think that hitting all new highs wouldn’t be material for market psychology and the election.

Anyone up for Dow 20,000?

The Combinatorics of Family Chaos

For those of you who read this blog regularly, you’ve likely noticed a lull in my posting.  That’s because, about two weeks ago, my wife & I welcomed a new addition to the family.  Given that the most common response to our decision to add a fourth child to the family has largely been “borderline insanity”, I felt it was appropriate to share some of my thinking on the complexity that comes with every new addition.

The Wrong Model: Linear

When a couple decides to have a second child, you are quickly inundated with advice on how to manage the complexity.  The most common refrain you hear is: “Don’t worry, you can still field man-on-man coverage.”  Another popular version of this advice is: “At least you’re not outnumbered.”

The implication here is that managing the family is fundamentally a relationship between parents & kids, like this:

Parental Ratio = # of Parents / # of Kids

With the implication that somehow, as long as the parental ratio is greater than or equal to one, you’ll be able to manage.

Unfortunately, I’ve found that this description of complexity dramatically understates the drama of real family life.

The Right Model: Combinatorics

Instead 0f focusing specifically on the number and types of nodes in the family graph, I think it’s more useful to think about the nature of emotional entanglements (aka “drama”) and understand that they tend to require at least two people, but can easily involve more.  As a result, the complexity of family life can be more accurately modeled as the number of two-party relationships in a family that can engage in drama.

Initially, a couple has exactly one potential pair:

  • Adult 1 <-> Adult 2

However, once you add a single child to the mix, you immediately add two more vectors of potential drama:

  • Adult 1 <-> Child 1
  • Adult 2 <-> Child 1

It’s worth noting that it’s sometimes unclear whether a three-party argument is truly a single argument or actually a combination of two or three two-party arguments, but let’s just roll with the simplified assumption for now that all drama can be decomposed to pair-based drama.

Pascal’s Triangle actually makes calculating this number for any size family trivial.  This means that:

  • Two family members (0 kids): 1 drama pair
  • Three family members (1 kids): 3 drama pairs
  • Four family members (2 kids): 6 drama pairs
  • Five family members (3 kids): 10 drama pairs
  • Six family members (4 kids): 15 drama pairs

It’s combinatoric, specifically in the form of:

family complexity  = # of family members  choose 2

Which is a fancy way of saying each new child adds a new relationship to the mix for every existing family member.  This sequence is also known as the triangular numbers.

For those of you who have or come from large families, let me know if this lightweight graph theory matches your experience.

Julia Elizabeth Nash

Julia Elizabeth Nash
Born 10.0 lbs, 21 inches
Single handedly increased Nash family complexity by 50%

Joining Greylock

Today, John Lilly put up a really nice note on the Greylock Partners blog officially welcoming me to the firm.  Needless to say, I’m both honored and excited to be joining such a great team.

We’re fortunate to be witnessing the explosive growth of not one but two incredible new platforms for consumer products and services: social and mobile.  Both are literally changing the fundamental ways that consumers interact with devices, and are rapidly changing the dynamics for building successful new products and services.  After spending the past four years helping to build out social and mobile platforms, I can’t wait to partner with entrepreneurs to help them build out the next generation of products and companies over them.

Over the past few years, I’ve shared a number of insights here on this blog about building great products and companies.  Here are a few that are worth reading if you are curious about how I think:

And of course, the most appropriate for this announcement:

For now, I just want to say thank you to Reid, David, John and the entire Greylock team.  I can’t wait to get started.

How To Make A Great Tech T-Shirt

Late last year, I happened to write one of my most popular blog posts ever called: Why T-Shirts Matter

One the best t-shirts: LinkedIn Breast Cancer Awareness T-Shirt 2010

Since then, this blog post has been viewed over 36,000 times.  It has been referenced from Hacker News, TechCrunch, Zazzle, and many other blog posts.

Ironically, that blog post has a cliff hanger at the end of it:

It turns out that this is a lot harder than it appears.  Mario always tells me my blog posts are too long, so I’m going to save this topic for the next post…

So Where Is It?

One of the most common questions I get now is “when are you going to write the post on how to make great tech t-shirts?”  Let’s be frank – it has been over eight months since the original post.  Procrastination is one thing, but at this point you’ve got to wonder whether or not this is a Duke Nukem situation.

One Post or Eight?

One of the reasons I haven’t been able to put this post together is that there really is a lot to cover.  I’ve spent quite a bit of time thinking about this problem, and as a result, I’ve accumulated quite a bit of content on it.

So I’ve made a decision.  Rather than tackle this beast all at once, I’m going to turn this into a theme for this week.  Every day, I’ll post another aspect of how to make a great tech t-shirt.  At the end, I’ll add a summary post for those of you who prefer cliff notes.

How To Make a Great Tech T-Shirt

  1. Introduction
  2. Goals: Why Are You Making the T-Shirt
  3. Metrics: How Do You Measure Success
  4. Quality: Picking the Right T-Shirt
  5. Design: Styles That Work
  6. Execution: Avoid the Camel
  7. Operations: Collecting Sizes, Ordering & Distribution
  8. Summary: How to Make a Great Tech T-Shirt

Tomorrow, I’ll begin the series, adding links here as an index.  Can’t wait to get started.

Psychohistory: 2010 in Review

The stats helper monkeys at mulled over how this blog did in 2010, and here’s a high level summary of its overall blog health:

Healthy blog!

The Blog-Health-o-Meter™ reads Wow.

Crunchy numbers

Featured image

The Louvre Museum has 8.5 million visitors per year. This blog was viewed about 440,000 times in 2010. If it were an exhibit at The Louvre Museum, it would take 19 days for that many people to see it.


In 2010, there were 23 new posts, growing the total archive of this blog to 698 posts. There were 10 pictures uploaded, taking up a total of 1mb. That’s about a picture per month.

The busiest day of the year was January 4th with 2,735 views. The most popular post that day was Café World Economics: Profit & Cafe Points.

Where did they come from?

The top referring sites in 2010 were,,,, and

Some visitors came searching, mostly for ntfs mac, mkv to mp4 mac, hardest material, convert mkv to mp4 mac, and ntfs for mac.

Attractions in 2010

These are the posts and pages that got the most views in 2010.


Café World Economics: Profit & Cafe Points October 2009


How to Convert MKV to MP4 on Mac OS X March 2008


How to Mount NTFS Drives on Mac OS X with Read/Write Access May 2007
13 comments and 2 Likes on


How to Convert FLAC to Apple Lossless (MP4) on Mac OS X March 2008


How to Delete Individual Backups from Apple Time Machine March 2008

I Need to Blog More & Tweet Less

I’ve come to a painful realization in the past few months:  I need to blog more and tweet less.

Don’t get me wrong – I’m a huge fan of Twitter.  I’ve learned a lot from them from both a user-perspective and a product-perspective.

The problem, however, is that tweets are ephemeral.  They offer an interesting combination of news sharing, brief commentary, and even a smattering of public dialog.  Unfortunately, they dissipate like snow flakes on a warm windshield.

I’ve been posting on the blog for several years now.  Almost 700 posts total.  But there is no question that my blogging activity has dropped considerably as I’ve tweeted more.  This is my first blog post in over a month.

And where are those tweets now?

In 2006 I wrote a thoughtful, but brief blog post about the Orion program, and the reinvigorated plans to establish a permanent presence on the moon.  A few weeks ago, President Obama put forth a proposal to kill the program.  I tweeted several times about it… but no blog post.  It’s sitting on a “to do” list of blog topics that I haven’t completed.

Does it matter?

I suppose it depends on the reasons that people have for blogging.  For me, blogging serves multiple functions:

  1. Blogging allows me to collect and share opinions about topics of interest (e.g. The Real eBay Magic: Irrational Commerce)
  2. Blogging allows me to demonstrate my interest / skills around a topic (e.g. The Personal Economics of Farmville)
  3. Blogging allows me to share knowledge publicly (Roth IRA Loophole: Everyone Can Qualify in 2010)
  4. Blogging allows me to keep a diary of topics of interest (The Self Organizing Quantum Universe)
  5. Blogging allows me to personally experiment with social media (Category: Blogging)

Unfortunately, I’m worried that the trade off between tweeting and blogging is having a significant long term impact on many of these goals.

My working theory is that Twitter is influencing me to blog less in two ways:

  1. It’s real time. As a result, I’m more likely to comment on something during the day, rather than waiting until the evening to blog about it after work.  But, once I’ve commented, the pressure to blog about it lessens.
  2. It’s where I get my news. As I’ve started depending on Twitter more for news than Google Reader, my old workflow of going through blog posts and articles, finding topics of interest, and then blogging has been broken.

Now, Twitter has its own value.  In terms of traffic generation, I find it phenomentally effective.  It has also become my primary conduit to gain environmental awareness of topics both personal and professional.  Twitter has also enhanced my professional reputation in a number of circles – circles that rarely if ever discovered by blog.

As a result, while I’m still going to tweet frequently in the coming month, I’m also going to make a renewed effort to blog more frequently over the next 30 days.  At minimum, I’m going to shoot for 1-2 posts per week, to get some rhythm back into the exercise.

I’m also going to experiment with some different tools and features to see if I can’t help turn topics that I find interesting enough to tweet about into topics I’m interested enough to blog about.

The Identity of Fake Leonard Speiser is Revealed!

Too much fun.  Tonight, we revealed the identity of Fake Leonard Speiser to, well, the real Leonard Speiser.

The key to obfuscation was simple: there was no one Fake Leonard Speiser.  A group of people who have worked with Leonard before all had access to account.  Consider it a form of “Twitter Improv”.

Yes, this is the kind of fun we have in Silicon Valley.  It’s because we’re geeks.

See below for the kickoff email.  We had fun with this all weekend.  I hope Leonard (and fans) did too.  I’d like to think that even though Fake Leonard was just around for a few days, he was starting to develop a real personality.

Goodbye, Fake Leonard.

From: Adam Nash
To: Elliot Shmukler, Chris Yeh, Bart Munro, Ben Foster, Shri Mahesh, Michael Dearing, Kenny Pate
Subject: Welcome to the Fake Leonard Conspiracy
Date: Fri, 25 Sep 2009 11:10:37 -0700

Merely by reading this email, you have been inducted into the Fake Leonard Speiser conspiracy.

Yesteday, Leonard made the mistake of issuing this tweet:

Clearly, this was a desperate cry for a prank.  We will oblige him.

Behold, Fake Leonard Speiser:

Instead of just one of us making up fake lines from Leonard, we are *all* going to contribute.  Kind of like a live, Twitter improv.

Here is the commitment:
For the next few days, every one of us will make *at least* one tweet from the Fake Leonard account.  Don’t worry about being consistent with the tone of everyone else too much – just shoot out lines that you can imagine Leonard saying.

Follow @fakeleonard, and tweet/respond/retweet his posts, to help get his followers up.  If someone wants to run around and follow a broad swath of his social network, all the better.

This is all in good fun, so nothing too personal or offensive.  🙂

The account password is:

Please try to make your first tweets today… I got mine in.

Email me with questions.

Update: I’ve been reminded that this is the second online gag I’ve played on Leonard Speiser… in the first, the co-conspirator was

More Farmville Economics: Treeconomics

Wow.  The traffic from the first two blog posts on Farmville has been high.  In fact, the Zynga blog even picked up the two articles.  Very flattering.

I was all set to write a post tonight on the economics of trees in Farmville… but then I caught Pablo’s post on “Treeconomics”.

Brilliant.  Leveraging some of the work I had done, he does a evaluation of a 16-square of trees in terms of “yield” vs. crops.  Very interesting, confirming that a 16-square of Date trees can compare very favorably to almost everything. Before we continue diving into the games, lets come back out into the real world, trees are good for the environment, but if you really need to get them out of your way and plant them somewhere else, then click here to get the best prices on stump grinding from this company. Now back to business…

I’m going to have to think about this a bit more – I want to build a model where I incorporate a few additional factors:

  • The “down payment” for trees.
  • The freedom to never have to “plow” or “plant” again. (value of time)
  • The freedom from working capital for seeds on an ongoing basis.
  • The removal of “withering risk”.  Crops wither after 20% of their growing time, yielding a complete loss of the capital to plow & plant.  Trees never wither.
  • The lack of experience points from trees
  • Incorporate the data from all the trees, not just the ones you can buy.

I’ll still write a follow up here, but tonight there is no need.  Check out this table from Pablo as  sample:

Cost Revenue/Harvest Days to Harvest Daily Revenue Daily Rev/ Invested $ Days to Payback
Date $800.0 $69.0 3 $23.00 2.88% 35
Lime $750.0 $75.0 5 $15.00 2.00% 50
Lemon $475.0 $41.0 3 $13.67 2.88% 35
Peach $500.0 $47.0 4 $11.75 2.35% 43
Fig $350.0 $33.0 3 $11.00 3.14% 32
Plum $350.0 $30.0 3 $10.00 2.86% 35
Orange $425.0 $40.0 4 $10.00 2.35% 43
Apple $325.0 $28.0 3 $9.33 2.87% 35
Cherry $225.0 $18.0 2 $9.00 4.00% 25

And this one:

Daily Profit Total Profit Initial investment Residual Value Profit
Super Berries $900.0 $81,000.0 $81,000.0
Date tree square $368.0 $33,120.0 $12,800 $640.0 $20,960.0
Tomatoes $174.0 $15,660.0 $15,660.0
Raspberries $132.0 $11,880.0 $11,880.0

Too cool.

Now go read it.

Updates: I’ve now posted additional articles on Farmville Economics: